If you defined the ServletContextListener by the annotation @WebListener on the Undertow container server when you stops the Undertow server the ServletContextListener's contextDestoryed method is not called
You can work around the problem by providing a custom Undertow factory that returns a custom Undertow container that overrides stop() to also call undeploy()
the spring boot before the 1.5.13.RELEASE has this bug and will fix the next version in Milestone 1.5.x
issure description:spring-projects/spring-boot#13134